Stop 1: Montelle WineryAt the Weinstrasse (literally “wine street”) end of the valley outside Augusta, vintners produce whites that rival those of their European brethren. Rock and blues musicians hold court on the hilltop terrace at Montelle Winery, arguably one of the most picturesque spots on the route. Try the Chardonel, a dry, fruity white made from Chardonnay grapes crossed with the cold-tolerant Seyval. montelle.com or 888-595-9463

Stop 2: Mount Pleasant WinerySnag a seat on the patio, high on the limestone bluffs overlooking the Missouri River Valley, and sip a glass of the winery’s award-winning Norton, a dry red made from Missouri’s state grape. mountpleasant.com or 800-467-9463

Stop 3: Vintage Restaurant at Stone Hill WinerySate your palate at these restored stables and carriage house in the heart of 2.3-square-mile Hermann, a town that lauds its German pedigree with every bite of Knackwurst, späztle, and schnitzel. stonehillwinery.com or 573-486-3479

Stop 4: Adam Puchta WineryLearn how winemaking began in Missouri in the mid-1800s at the Adam Puchta Winery, just southwest of Hermann, near the banks of Frene Creek. adampuchtawine.com or 573-486-5596

Stop 5: Hermann HillStep into the Bavarian storyscape at this European-style inn, complete with half-timbered exteriors, in-room fireplaces, and sweeping views of the Missouri landscape. hermannhill.com or 573-486-4455; rates start at $190.